1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69627413, compound

HRID 244369Notes

Reaction equation

HRID 244369 reaction equation
Cl.[CH:2]([N:5]([C@@H:32]1[CH2:37][CH2:36][CH2:35][NH:34][CH2:33]1)[C:6]([C:8]1[C:9]([C:28]([F:31])([F:30])[F:29])=[CH:10][C:11]2[O:16][C:15]([CH3:18])([CH3:17])[C:14](=[O:19])[N:13]([CH2:20][CH2:21][NH:22][C:23](=[O:26])[CH2:24][CH3:25])[C:12]=2[CH:27]=1)=[O:7])([CH3:4])[CH3:3].[C:38]([NH:45][C@H:46]([C:50](O)=[O:51])[CH:47]([CH3:49])[CH3:48])([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:18][C:15]1([CH3:17])[C:14](=[O:19])[N:13]([CH2:20][CH2:21][NH:22][C:23](=[O:26])[CH2:24][CH3:25])[C:12]2[CH:27]=[C:8]([C:6]([N:5]([CH:2]([CH3:3])[CH3:4])[C@@H:32]3[CH2:37][CH2:36][CH2:35][N:34]([C:50]([C@@H:46]([NH:45][C:38](=[O:39])[O:40][C:41]([CH3:42])([CH3:44])[CH3:43])[CH:47]([CH3:49])[CH3:48])=[O:51])[CH2:33]3)=[O:7])[C:9]([C:28]([F:30])([F:29])[F:31])=[CH:10][C:11]=2[O:16]1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 83693Boc-L-ValineHCID 67511771HCID 67511771, compound

Product 1

HCID 69627413HCID 69627413, compoundYield 113.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

To N-isopropyl-2,2-dimethyl-3-oxo-N-[(3R)-piperidin-3-yl]-4-[2-(propionylamino)ethyl]-7-(trifluoromethyl)-3,4-dihydro-2H-1,4-benzoxazine-6-carboxamide hydrochloride (300 mg) were added N-Boc valine (158 mg), WSC (210 mg), HOBt (150 mg), triethylamine (0.30 ml) and chloroform (5 ml), and the mixture was stirred at room temperature overnight. After the reaction is completed, the solvent was concentrated, and the obtained residue was purified by column chromatography (hexane:ethyl acetate=1:2) to give the desired title compound (440 mg) as white amorphous.

Workup

  1. concentrationthe solvent was concentrated
  2. customthe obtained residue was purified by column chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-434e9a04dbd54f118a23d19bf7ece134
Source dataset
uspto-grants-2014_02
Patent number
US08658639B2

Reaction notes

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